(S)-9-(5-bromo-2-oxo-2H-pyran-3-yl)-2-methylnon-8-yn-3-yl acrylate | 907157-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-9-(5-bromo-2-oxo-2H-pyran-3-yl)-2-methylnon-8-yn-3-yl acrylate
• 英文别名: [(3S)-9-(5-bromo-2-oxopyran-3-yl)-2-methylnon-8-yn-3-yl] prop-2-enoate
• CAS: 907157-53-3
• 化学式: C₁₈H₂₁BrO₄
• 分子量: 381.266
• InChiKey: NMNBHVKTLHVNJF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-9-(5-bromo-2-oxo-2H-pyran-3-yl)-2-methylnon-8-yn-3-yl acrylate 以 甲苯 为溶剂， 反应 14.0h， 以64%的产率得到(1S,8S,11R,13R)-17-Bromo-8-isopropyl-9,14-dioxa-tricyclo[11.2.2.0^1,11]heptadec-16-en-2-yne-10,15-dione
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g
• 作为产物：
  描述：

  (R)-异丙基环氧乙烷 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 potassium hydride 、 1,3-丙二胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-9-(5-bromo-2-oxo-2H-pyran-3-yl)-2-methylnon-8-yn-3-yl acrylate
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g

文献信息

• Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones
  作者：Jeong-Taek Shin、Sung-Cho Hong、Seunghoon Shin、Cheon-Gyu Cho

  DOI：10.1021/ol061198g

  日期：2006.7.1

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.